There might not really be a "Last Train to Clarksville," but if you need to get to Tooth Acres, the Customs House, or Strawberry Alley, you might ask an old-timer.

Just don't try to walk to Clarksville's most obscurely named landmarks. Toe Acres is just a memory now, and sore feet will make climbing Boot Hill a headache even Head Acres can't cure.

The Queen City of Clarksville is full of quirky places or normal places with quirky names, some older than others. Here's how they got those monikers to begin with.

Tooth, Toe and Head Acres

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Head Acres, next to Tooth Acres, was owned by a barber. Toe Acres, owned by a podiatrist is gone now.(Photo: Stephanie Ingersoll/The Leaf-Chronicle)

The signs along Madison Street have likely inspired the imagination of children or even adults who happened to notice them.

Two of the three signs still stand in front of normal-looking homes, though one now serves as a church now.

Darlene Ward got married at Head Acres, where her in-laws lived for about 23 years. Her father-in-law, Bo Ward, bought the home from a podiatrist, who as a joke had called it Toe Acres.

But that just didn't jibe with Ward's career.

"He was a barber and owned Bo's Barber Shop by Gate 1 (at Fort Campbell.)" So he changed the name to Head Acres.

The home was sold to a church, but the "Head Acres" sign still stands, right next to Tooth Acres, on a homestead owned by a dentist.

Customs House not customary at all

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This design for the Customs House and post office was rejected at first but now makes it one of Clarksville's star attractions.(Photo: Stephanie Ingersoll/The Leaf-Chronicle)

These days, the Customs House Museum & Cultural Center in downtown Clarksville is one of the most revered and photographed landmarks in the city.

But before it opened in 1898 as a post office and customs house, to collect duty on imported or exported goods, the design riled up so many citizens, it was re-designed twice.

Plans were submitted by architect William Aiken in 1897, and groundbreaking began that year without public approval.

The Daily Leaf-Chronicle wrote, "Clarksville does not propose to accept the crazy plans that have been submitted from the Architects Office for this building. They have been seen by certain of our citizens who say that a building constructed by such plans would be simply an architectural absurdity and a public laughingstock."

That battle is still chronicled at the museum today.

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The second design of the Customs House, rejected as too boring, are still on display at the building, now home to a museum.(Photo: Stephanie Ingersoll/The Leaf-Chronicle)

After a second design proved far too boring, the original plans were adopted again, with its 20 dormers, arched windows, pinnacles, angles and four copper eagles perched on the corners.

The original spire, ripped from the building in the 1999 tornado was found several blocks away and is on display in the lobby. The building's architecture helped land it on the National Register of Historic Places.

Springing eternal

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There is a capped off Spring on Spring Street but it hasn't been used since an emergency in the 1930s.(Photo: Stephanie Ingersoll/The Leaf-Chronicle)

It's called Spring Street, but unless it's raining, odds are you won't find much water there. That's because the inspiration for the street's name doesn't gurgle above ground anymore.

Located beside the Clarksville Police Department's main office on Commerce Street, a sign recalls a time when the water there was vital to the city. The town spring was used by early settlers but later capped and diverted to the nearby Cumberland River.

When disasters hit in 1937, leaving Clarksville without a water supply, the spring was uncapped for emergency use, but it was later capped and sealed up again.

Strawberry fields

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Strawberry Alley was named for the woman who used to have a large patch there.(Photo: Stephanie Ingersoll/The Leaf-Chronicle)

The seeds that gave Strawberry Alley its name are old indeed.

According to the Montgomery County Historical Society, the street was built across a large strawberry patch owned by Lucinda Elder, the wife of Clarksville's first mayor.

Once called Poverty Row in the mid-1800s, the name Strawberry Alley stuck until the end of World War I, when the street was extended and renamed Legion Street.

The name Strawberry Alley made a comeback in 2008, between First Street and Second Street.

Don't expect to find too many berries there. These days they are mostly limited to the flavored alcohol or smoothies found at nearby restaurants. But there's plenty of straws.

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Strawberry Alley in downtown Clarksville was once the home to a large strawberry patch(Photo: Stephanie Ingersoll/The Leaf-Chronicle)

Boots not on the ground anymore

Almost any native Clarksvillian can tell you where to find Boot Hill.

The steep incline leading from Riverside Drive to New Providence got its nickname because of the Acme Boots store that used to be located there, not far from Fort Defiance.

There was also a huge boot sign to get the attention of passersby.

The Acme Shoe Manufacturing factory was located on Crossland Avenue, and Acme was one of the city's largest employers — a godsend during the Great Depression. Originally a maker of baby shoes and footwear for children, it was renamed Acme Boots and became the largest maker of cowboy boots for several decades.

Acme Boot Manufacturing began hiring workers for a new manufacturing plant in Puerto Rico in 1993 and closed its Clarksville plant, sparking protests and boot burnings.

The showroom on Boot Hill is gone now, too, but if you decide to climb the hill, make sure you boots are made for walking.

Roads, more or less

Most motorists wouldn't complain about needing more roads. Some might say we need less. Some would put it on a sign.

Needmore Road is one of the longest in Clarksville and is used by thousands of people every day.

It intersects with a lesser-known and much shorter cousin, Needless Road, between Glenellen Elementary School and the Clarksville Speedway. Needless is only a few hundred yards and leads to a small neighborhood.

Who's behind these names? We Needmore information and not less.

Budding of the Leaf

The Clarksville Chronicle office, before the 1890 merger with The Tobacco Leaf.(Photo: Leaf-Chronicle files)

The Clarksville Chronicle started in 1808 as a weekly newspaper. Over the decades, competitors came and went, but one popped up in 1869 called The Tobacco Leaf, representing the city's powerful tobacco industry.

The Chronicle's response was that "our paper can advocate the tobacco interests as well as if it were named Tobacco Hogshead!" An intense competition continued for about 20 years.

But it didn't last. In 1890, the Tobacco Leaf bought the Chronicle. The staffs were combined, and the resulting publication was initially called The Clarksville Tobacco Leaf-Chronicle, later shortened to The Leaf-Chronicle.

A century later, when Hemlock Semiconductor's plans for a local polysilicon plant made big news, there was joking discussion about updating the industry-based name to The Polysilicon-Chronicle. Nah.

They got what you 'Needa

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The oldest advertisement in Clarksville proclaims "Uneeda Biscuit." The National Biscuit Company later became Nabisco.(Photo: Stephanie Ingersoll/The Leaf-Chronicle)

Despite the huge sign adorning its side, you're not likely to find a biscuit or undertaker at the corner of Main Street and Public Square (once called Telegraph Street).

You will find one of the oldest advertisements still visible in the city.